1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach | Zendy

Lin Wang | Zendy; Armido Studer | Zendy

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1-Trifluoromethylisoquinolines from α-Benzylated Tosylmethyl Isocyanide Derivatives in a Modular Approach

Author(s) -

Lin Wang,

Armido Studer

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.7b02882

Subject(s) - chemistry , isocyanide , catalysis , combinatorial chemistry , reagent , alkylation , organic chemistry

The preparation of various 1-trifluoromethylisoquinolines from α-benzylated tosylmethyl isocyanide derivatives and the commercial Togni reagent using a radical cascade is reported. The starting isocyanides are readily prepared in a modular sequence from commercial tosylmethyl isocyanide via sequential double α-alkylation, and the radical reaction proceeds under mild conditions with high efficiency without any transition-metal catalyst via electron catalysis. This valuable protocol has been successfully applied to the total synthesis of CF 3 -mansouramycin B.

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